The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Attempted synthesis of polypeptides by condensation of amino acid and peptide esters I》. Authors are Brockmann, Hans; Musso, Hans.The article about the compound:2-Bromo-3-methoxypropanoic acidcas:65090-78-0,SMILESS:O=C(O)C(Br)COC).SDS of cas: 65090-78-0. Through the article, more information about this compound (cas:65090-78-0) is conveyed.
Methods are given for fractionation of the amino acid, peptides, and their Me esters in the cases of glycine (I), alanine (II), and serine (III). After several months at room temperature, either dry or in various solvents, I Me ester gave mainly tetraglycine Me ester (IV) and I anhydride (V), as well as some pentaglycine Me ester and hexaglycine Me ester. In H2O, MeOH, or EtOH the product was mostly V. Condensation of II Me ester, either dry or in MeOH, gave mainly II anhydride. In H2O hydrolysis to II occurred. III Me ester (VI), dry or in various solvents at 20°, gave after several weeks mainly III anhydride (VII), with some III and unchanged VI. Vacuum distillation of VI gave VII, III, MeOH, NH3, H2O, II, and traces of III peptides. VI was kept in vacuo at 20°, warmed 1 h. to 75°, refluxed 10 h., or kept at 20° in pyridine or HOAc. In each case the major product was VII, and III, VI, and some III peptides were present. IV kept at various temperatures, dry or in H2O or MeOH, was either unchanged, hydrolyzed, or converted largely to unidentified products.
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Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia